New York Heist
by sarinspill
Summary: It's the 1930's and Castiel just got promoted to Detective in New York City, the opportunity of a life time. At the same time, Dean Winchester just received the biggest hit yet as the Mafia's go to hit man. Target being, Castiel Novak.
1. Chapter 1

Hi there, everyone. First off, I want to thank the tumblr community for beta reading this and helping me come up with the idea. more specifically, mishaminions for originally coming up with the plot. Next, this is a work of fiction (obviously) so I own no rights to character names and such. Thanks for reading, I'm excited to start a new story with you guys.

xx

Castiel Novak. He was the new kid with a reputation. The guy from Chicago, they started calling him. It was the gossip of NYC's police department. Castiel had just snagged a serial murderer with five deaths under his belt when the offer to transfer came up. The Chicago Thunder, they started calling the murderer. Castiel could still taste the stale coffee he drank every single night, going through files after files of evidence and witness accounts. When the day came that Mr. Novak caught The Chicago Thunder, he was offered a new position in New York City. The pay was barely any different and he had to start from scratch but it was an opportunity he definitely could not miss.

Dean Winchester, the golden boy of The Family Business. It started while in New Jersey, living in shady streets with his good for nothing of a father. Dean always looked for ways to make his and his brother's lives better. It was a fist fight with a neighboring gang member that led him to where he is now. Dean Winchester was a hit man for the Mafia, the final warning for the customers of The Family Business. Dean never saw himself as a murderer but as a repo man. He simply took what was owed, by force if necessary. He rarely ever had to bump off anyone but in the end, he knew what he had to do. His goals were simple. Protect his brother, protect his name, and never ever get caught.

December 7th, 1934.

There were reports of Dean Winchester entering a building located at Alderton Street at approximately 5:00PM. Agent De Luca and Agent Novak were sent to investigate. The following report was compiled from witness accounts, reports from both Agents and other investigators.

xx

3:00 PM

"It's simple, Dean. Collect my check. This punk tells me he's one smooth dealer, a real darb. But he hasn't paid for this month's favor. Pick up my check, will you? Bring Sammy if you want, when's that boy gonna get in the business anyway?" Luis mumbled, lighting his cigar and giving his lighter to the girl whose name always escapes Dean's memory. The beads of her necklace clicked and chimed as she walked, the soft tapping of her heels dissipating. He knew she wouldn't come back, the minute their talk gets to the business, the girls always leave. It was never their conversation.

"Sam? I'm not sure; he's not one for the league. He's more into going to school, bit of a crumb if you ask me." Dean replied, his hands stuffed knee's deep into his pockets. He hated talking to his bosses as if they were his friends, they never were. Luis Santiago was a mob boss; he wasn't some guy you sip beers with. So when he was asked to come meet him for a new assignment, he silently obliged. The new target was a Polock name Andrzej Borkowski, who asked for protection from an enemy shop keeper. Every month he was asked to pay a very easy $100 for the protection but lately, he'd been slacking with the payments. It was time to collect and that was why Dean was there.

"Well, tell the boy to go with you. See what he thinks. Andrzej is a weakling, he shouldn't be that hard to snub out if necessary. Am I right, Dean?" Luis said with a giant puff of smoke, it slowly seeping from his nostrils like tendrils of thread, floating in the wind.

"Of course, Sir." When Luis flicked his wrist for Dean to leave, he made his way to his car. Finally he could return home to his apartment with Sam.

"Sammy. Meet me in my room, will you?" Dean shouted while picking up an apple from the counter. Their apartment was nothing special, a hole in the wall in a building that was made twenty years ago. The apartment complex was packed tightly with identical buildings all down the street, with paper thin walls and drippy sinks. It had two bedrooms and one bathroom, a kitchen that doubled as their living room so they didn't really have one. Dean took his hat off and put it on their coat rack, making his way to his room and sitting on the creaky bed. The room was small and empty; the older of the two brothers didn't bother to bring things with him when they moved from Paterson.

Sam's door to his room opened and closed, the boy inside now standing at Dean's doorway. "What's up?" He asked, looking around the room. Dean stared at him for a minute, always forgetting how much he's grown since high school. His arms and legs grew lanky while his hair long and shaggy. It wasn't that he liked the look; it was more they never got around to getting it cut. "I had a meeting with Luis today... he asked about you." Dean murmured while sprawling across the bed, one arm behind his head and the other out so he can keep eating his apple.

"Okay...?"

"Well, he wanted you to come with me on this next hit. I told him you weren't really into this kind of thing but you know... I figured I'd ask you before I make any decisions for you."

"Oh... what's the profile?" Sam asked while walking over to the bed and sitting on the edge, his head craned over to look at his older brother.

"Some Polish guy in Rego Park who wouldn't pay. Couldn't be that hard." Dean said in between bites of his fruit, staring at Sam in question. The younger brother looked like he was thinking really hard, his brow wrinkling a bit. Dean always associated this look with Sam doing his homework in middle school, still unsure on how to do certain division questions. It was one of his fondest memories, helping his Sammy out with his homework even though he dropped out of High School a long time ago and didn't know long division himself. It scared Dean to think that his brother might be put in a situation where he could get hurt like following a hit but this assignment didn't look like it had much of a threat to it.

"Sure... I'll go."

xx

4:30PM

Castiel was just barely done unpacking at his desk, located in the farthest corner of the room, when Mr. Hiddleton came over to pat his shoulder. "So! Castiel Novak. How's the move? Good I hope. But Mr. Novak, I'm afraid we're going have to get you on the move asap. We just got word that a big shot hitman is going to go do his thing at Rego Park." Mr. Hiddleton said while walking him over to his office. Castiel was confused as to why he was given such a big assignment so soon in his career with the Department but didn't question it, never did. In the end, they knew what was best for the community and for the mission.

"Snag him if you can. It's a big responsibility so I'm going to pair you with someone who has been following this boy for awhile now. Frank De Luca, one of the best in the force. He'll show you the ropes. Find him, get going. Hurry before you miss him." Hiddleton sat down and started looking over papers while Castiel made his way out, walking over to his new partner's desk. The new building was much bigger than the one in Chicago and was located almost in the middle of New York. It was a lot different and had some culture shock after he had made his way to the state.

After finding Frank, he introduced himself to the Italian. He had floppy dark hair, pushed back with a slick of grease like many of the other men in New York. Frank was thin and lanky, his uniform appearing loose on him.

"Castiel Novak, right? You're my new partner." His thick Italian accent dripped through his dialogue, Castiel stumbling a bit to understand him. Not many people had accents so thick like his in Chicago, so when he moved to New York, he felt foreign in many cases. Castiel nodded at Frank and shoved his hands into his over coat's pockets.

"Alright well, we better get out of here right away. The Golden Boy will be there any minute." Frank grabbed his coat from his chair and they made their way out of the busy building.

"Golden Boy..?" Castiel started, looking at Frank silently as they made their way to an undercover car.

"Yeah, Dean Winchester. I take it you didn't get a chance to read his file? I've been on this guy for years; this is the closest I've ever gotten to him. He's from New Jersey, a real smooth talker kind of kid. He got the nickname Golden Boy from the press cause he's the go to for the Mafia for a hit. He's quick, precise, and never leaves a trail. The perfect assassin." Frank joked in the end, making their way to Rego Park, a small section near Queens.

5:00PM

"I'm sorry Mr. Borkowski but we gotta be quick with this, Sammy's got to study." Dean said after handing his brother the money that was owed. Right after Dean pulled out his favorite pistol, emptying a bullet into the desperate and shaking man. Sam was about to protest but he knew the way of his brother's employer. It had to be done; they had to set an example that this behavior wouldn't be tolerated. He turned his head as the gun shot, his lips forming a thin line. Dean looked from the dropped body to Sam, his brow stitching together in confusion, "What's up Sam?"

"Nothing... let's go." Sam started to walk out but Dean pushed him back into the room after hearing the door of the apartment complex's main entrance swing open.

"Sam, fire escape. Now. Go, go." Dean watched his brother start his way out and the hurried footsteps of two men coming up the stairs. The older brother closed the door quickly, closing the bolt lock before making his own way to the fire escape. Just as he stepped out the window adjacent to the door, it swung open to reveal one cop that Dean knew for certain and another that was new to him.

"Maybe next time boys." He winked and made his way down the fire escape, Sam already jumping into Dean's car and starting the engine. He heard some gunshots above him with exclaimed cusses, smirking to himself while they sped down the street.

xx

"Maybe next time boys." The criminal said with a wink and disappearing from his sight. Castiel was awestruck, to say the least. Dean Winchester, 'The Golden Boy', was nothing like he had expected. He was probably the same age as him, if not a few years older. But something about him, his looks made the detective curious.

"We fucking missed him? How did we miss him!" Frank yelled, shooting at the window before running over to it and looking down. Castiel looked down at the body of a man that had yet to be identified, careful not to step into the puddle of blood. He heard Frank curse and shout, looking around the dingy and smelly apartment. With a heavy sigh, he put his gun back into its holster and made his way out.

"We better get going, Frank..." He muttered before finally leaving the room. Dean's face was still fresh in his head and it nagged at him. The one thing Castiel was not expecting was for him to be so young. It stunned him, leaving him pondering his features. If he wasn't a top wanted criminal, he might have even been interested in him. He heard De Luca start to go off on how it seemed like Dean had a partner with him but Castiel barely listened on their way back to the station.

xx

"It was too close, Winchester! Too close for comfort!" Luis started, waving his giant cigar around in exasperated movements, leaving a trail of smoke everywhere, "Don't get me wrong, I'm glad you got the dough. But you had two pigs on you and that's two too many!"

"I know, sir, I'm sorry. What do you want me to do...?" Dean had started, unsure of how to exactly handle the situation. Everything on their part went according to plan. It was just some other force that messed up with the other day's heist.

"I have an idea. De Luca we can take care of, he'll be easy to take out. His partner though, I got information on him. He's a new kid from Chicago. You remember Kenny Blocker? He's the shit that got him arrested. Right after that, he got some big shot murderer in the cage and was moved here." Luis took a long drag from his thick cigar, a wicked smile brimming, "You're the only one I can trust to get rid of him, Dean. He could be a threat. Eliminate him and come back. I will promise you; after he's gone... money will not be an worry for you in a long time."

Dean's back straightened and he nodded his head while puckering his lips. Another hit but this time it was not going to be easy. The cops were some of the hardest to get rid of and the most dangerous to live through afterward. But money was tight back home and if Luis kept his word, like he always did, than he knew that he was going to get paid extremely handsomely.

"You've got yourself a deal." Dean muttered in reply.


	2. Chapter 2

First off, thank you so much everyone! I got a bunch of emails saying alerts and reviews, I don't think I've ever been so happy. I hope this chapter is as good for you as it is for me. This chapter has some sexual themes in it so if you're against it, don't read it. Enjoy!

xx

If looks could kill, Castiel would be like a rusty spoon at this point. There were bags under his eyes and his hair was slick as grease. The man had barely slept in the past week, only thinking about one thing all day. Dean Winchester, the Golden Boy of New York. Every time he even pictured his face, he wanted to rip his hair out and scream. He wasn't exactly sure why he kept thinking of him either, it just happened. Like while writing up a report on a nearby shooting, he thought of him. While tying his shoes, he thought of him. It was eating him away slowly and made him hazy. One thing was for certain, this was certainly the last thing he expected when offered to be transferred to New York.

Meanwhile, Dean was watching his target like a hawk. Every day he sat in an empty apartment across the street of Castiel's, watching him eat and sleep. The first rule of such a big hit like this was to watch their pattern. See their weakest moment to strike. Castiel was a very interesting person, Dean could admit. Always working hard and never taking a minute to stop and breathe. He sat in the empty apartment for an entire day waiting for him to get back from the station but he didn't get home until six in the morning the next day. Dean was packing up, putting on his hat and everything when the detective finally crawled into his home with a bundle of folders and papers under his arm. He watched him, bending down to stare out the window and into his. The first thing Castiel did was flick on the coffee maker, expecting another sleepless night to work. Dean wrinkled his nose and sat back down on the crate he positioned in front of the window, his jacket dragging on the floor a bit. He didn't leave then until 12 in the afternoon when Castiel fell asleep on his kitchen table while typing on his typewriter.

Sometimes Sam will come with him, on the days that he didn't have class. He would ask a bunch of questions like what did the name Castiel mean or if he would ever get home from the station. Dean only rubbed his eyes with his hand and dragged it down his face, still staring out the window.

"So this is what you do? Sit around and watch another guy live his life?" Sam asked, reading a five cent comic that Dean had picked up earlier.

"Yeah, Sam, I do." He snapped back, tired of his questions and snarky comments. He closed his eyes and sighed, waiting for the moment when Castiel would come through his front door. Any kind of distraction from his brother's questioning gaze is the best distraction.

"So when are you going to kill him?" Sam asked, hunching over a bit to whisper to Dean. Sam was taught well, always told to whisper or mumble this kind of talk cause you never know who is listening.

"Sam, you have to know something about hits on cops. They are smart, you can't just walk in there and bump him off. The quickest and safest way just so happens takes up the most time compared to any other hit." Dean whispered back, laying his elbows on his knees. Sam just responded with a shrug and leaned back on the chair they found in the hallway.

"Whatever you say, Dean..."

xx

Castiel swore he was finally starting to lose it because one day, he looked out his window and he saw him. Right across the street in the empty flats. He had to rub his eyes and blink before looking again and he was gone. He saw him hunched over, staring right back at him with an intent look on his face. For some reason though, it nagged at him. Throughout the rest of the day, he saw him just sitting there in the back of his mind. While eating a bowl of cereal on his bed, he convinced himself to go. He would go to the apartment and just look around. What was the worst that could happen, he would think to himself. Worst case scenario, Dean would actually be there. In which case, he brought his gun with him just in case.

Castiel trudged up the stairs silently, his heart beating faster than a locomotive. His head kept running through scenarios of what would happen. Like opening the door and finding no one there, just dust and dark corners. Then he would imagine Dean there, staring back at him with a gun in hand. None of them gave him comfort. If he wasn't there than Castiel would convince himself that he was losing it. If he was, then there was a mob boss hit man in the apartment complex across from him. Both end results made his skin crawl.

When he got to the apartment across from his own, 4C, he took in a gulp of breathe before turning the handle and walking inside. The detective looked around and found nothing. He let out a soft sigh and turned to walk out the door before he was pushed against it by a force.

"I wasn't expecting this, not going to lie..." The body behind him mumbled, his arm pressed to the back of his neck and his hand gripping Castiel's hand that held his gun, "I had a feeling you saw me but I didn't think you'd actually come over here."

He could hear his heart pounding in his ears, his eyes screwed shut tightly and his throat struggling to catch a breathe. Dean's body was pressed snug to his back, making all movement a struggle and nearly impossible.

"It'd be so easy for me to just rid you, right now. You even came with your own weapon. What do you say, shooting yourself in the head? Too much work from New York's hard crime, snapping under the pressure? Suicide is such a funny thing, you know?" Dean hummed in his ear, making Castiel twitch and struggle.

xx

The last thing Dean needed was the pig to come into the apartment; this was not the right place or time for the hit to go down. There was too many people in this apartment complex, too many people saw Castiel come into the building looking nervous. Dean would have left when he saw him coming but he was nervous of getting caught by him. Either way, he had a feeling that Castiel would find him today. At least in the current moment, he had the upper hand. His chest pressed flat to the detective's back, breathing in Castiel's smell. It almost felt surreal. He had been watching this exact man for almost a month now. He knew almost everything about him, his sisters and brothers in Chicago along with his favorite food. It drove him crazy. He realized just how insane he was when he felt a thrill from Castiel struggling against him.

"This isn't the time or place though..." Dean started.

"Don't kill me..." Castiel finally spoke, it sounded struggled and chocked back. He craned his head to look at Castiel's expression, his eyes red and mouth puffy from the abuse of being pressed against the door. Dean didn't know he had such blue eyes, staring right back at him. He almost got lost in them for a moment, staring at them for a moment or two. He was so close to him, he could almost taste his breathe.

"I'm not... not yet. Luis didn't like your interference, Cas. You made him really nervous. Not to mention you put one of our best men in the bird house. He really wants you dead..." Dean started, pressing himself harder against Castiel and watching as his eyes closed. But it wasn't from pain or fear, something else was there. Castiel started to bite his bottom lip and it made Dean's brow stitch together for a moment. Then it clicked.

"Oh... you are enjoying this, aren't you?" Dean smirked and moved his arm that locked his neck in place to grip his other hand and pin his hands above his head, "Do you like having me against you, Castiel?"

"Please stop..." Castiel whimpered, sounding out of breathe and ashamed. Dean continued to smirk and pressed his nose under his ear, gripping his wrists tight.

"Do you really want me to stop? I didn't know NYC's newest addition had a thing for men." Dean mumbled before looking down at his exposed neck, a sliver of skin escaping the collar of his white button up, "Just how far will you let me go, Cas?" He said before licking the soft slip of skin. Castiel immediately whimpered under him, biting his lip harder. Dean backed up for a moment, still holding his hands tightly.

"Turn around." Dean growled, looking over Castiel's body for a moment. Slowly and hesitantly, he turned around, his back pressed against the door. Indeed, he was hard under his slacks, the outline of his cock pressing against the fabric. Dean never really cared who he fucked, just as long as they did the job and he was enjoying the effect he had on the detective before him.

Dean leaned forward and pressed his lips roughly against Castiel, biting his lip for him. He earned himself a moan, taking the opportunity to shove his tongue into his mouth and taste him. Castiel had a soft hint of milk and vanilla in his breathe from the cereal, making Dean press harder against him. After a moment of hesitation, Dean took the gun in Castiel's hand and tossed it across the room before letting go of his wrists completely. His hands tugged at the tucked in edge of his shirt, Dean's hands roaming under the shirt to feel his skin. Castiel continued to whimper and moan into the heated kiss, eagerly reciprocating.

Dean pushed himself away quickly, though, snapping back to reality. He was making out with his hit, a detective that wanted to throw him in the bird house. He looked him over, breathing hard and mind racing. Castiel's shirt was rumbled and wrinkled, his lips puffy and his hair stuck up in every direction. He was breathing just as hard as Dean was, staring right back at him with the deep set of blue eyes. In a flash of movement, Castiel was out the door and running down the stairs. Dean was left standing alone in the apartment.

xx

The shower just wasn't cold enough, Castiel was still thinking of it. The way Dean was pressed against his back, the way he asserted control over him and the taste of his mouth. He scrubbed harder at his face at the thought, sighing loudly. He still didn't register what just happened, the one man he was trying to get arrested just had his way with him. The worst part was, though, that Castiel loved every second of it and wanted more. He groaned under the spray of water and turned it off, feeling hopeless. He stepped out of his shower and reached for the sink where he put his towel, drying himself off slowly while in thought. Whenever he was in a situation like this, where he felt so lost, he would think about his siblings. What would his older brother Sebastian or Gabriel do? Well, Sebastian would just have sex with Dean, that's for sure. Maybe Anna, what would Anna do? She was much more responsible than all of the brothers.

Castiel really missed his siblings, the only family he had besides Uncle Uriel. Sebastian was the oldest, than Anna, Gabriel, and ending with Castiel. They were always there for him, even when he told them that he was interested in men. Gabriel and Anna weren't very surprised, apparently, Sebastian being the only one who was the most shocked. He was convinced that Castiel was just waiting for the right girl. Not that he was only looking at kissing guys.

Castiel looked up at his ceiling, sighing heavily, "Lord, please guide me through these rough times and show me the right path..." He mumbled to himself before finishing off with drying off.

xx

Dean was sure Sam had every right to be worried about him, but he still refused to speak with him. Every morning that he woke up, he would hear Sam banging on his door to let him in. Ever since the day with Castiel, he'd just sit in his room and think. Think about everything, about his life with Sam and his job that he knows he has to complete. Dean didn't have time for dating nor did he feel like it was safe. Being a hit man, just as many people wanted him dead as he wanted them dead. So having a girlfriend or a boyfriend was dangerous, he could get a lot of people really hurt. Now the only person he could think about romantically just so happens to be the person that he needs to kill. He knew he was being timed as well, if he took too long than Luis would find him and star to question him. Dean rolled over and shoved his face into his pillow, feeling the need to scream.

This wasn't how he did things; Dean didn't sit around and think about boys. He was a man; he wasn't some teenage girl who had their first kiss. It was started to piss him off, how he was reacting to the kiss. He sat up quickly and left the room, making his way over to their kitchen. There, their hand me down radio sat. Dean quickly found the station that broadcasted the local boxing matches and sat on the counter, holding it in his hands. He needed to stop thinking about stupid detectives and more about the game.

It was never that easy though, Sam nearly running out of his room when he heard Dean leave his own.

"What's up with you? You've been locked in that room since yesterday morning!" Sam asked, standing across from Dean.

"It's nothing, Sam."

"If it was nothing than you wouldn't be moping."

"It's nothing, Sam, now drop it." Dean shot back, his eyes hard on his brother. He wasn't about to go and spill all of his emotions and feelings on his brother, it wasn't his style.

"Dean, something is obviously bothering you. You can't keep these kind of things pent up inside, it's not healthy." Sam argued, crosses his arms over his chest and pursing his lips some.

"Sam, if I wanted to tell you I would have already. Can you drop it so I can enjoy this lovely broadcast? Jeez..." Dean mumbled while looking at their polished wood floors. He saw from the edge of his eyes, Sam throw his hands up in the air before stomping back to his room and slamming his door shut. Dean had to stop himself from tossing their delicate radio, putting it down on the counter before jumping off and running his hand through his hair. He turned off the radio and grabbed his coat, making his way out.

xx

Castiel was typing a report on his type writer when he heard a knock on his front door. He looked up and stared at the door for a moment before standing up. He grabbed the handle but didn't turn it, hesitant for a moment. "Who is it...?" When Castiel heard no knock, he opened the door slightly. Instantly, it was pushed further open and a body made its way through. Dean stood there and kicked the door closed behind him. Castiel just stared at him, his mouth agape before he felt his lips on his once again. He couldn't help but melt into it, closing his eyes and standing still. Dean's hands moved his jaw, his fingers gripping the growing black hair.

"What are you doing here, Dean, you can't be here!" Castiel said against his lips after pulling back from the kiss but remained close to him. It felt good to once again have him near but he was conflicted, he knew what he had to do. He had to bring this man to justice; he can't just sit around and kiss him.

"Come on, Cas, just let it happen." Dean mumbled pushing him back until the back of Castiel's knees hit his couch. Castiel shook his head and opened his eyes to look at him, Dean staring back at him. His face was still close, his breathe brushing against him.

"I'm supposed to be arresting you..." Castiel chocked out, never breaking their locked gaze.

"I'm supposed to be killing you, what's your point?" Dean pressed his body against his, eager for contact.

"I barely know you!" Castiel started, backing away slightly.

"Oh please, you probably know more about me than my own brother. I know you're after me with De Luca, it's no secret."

"You know De Luca? Did you..?" Castiel asked with wide eyes.

"Kill him? No, I didn't. You were my target..." Dean mumbled, averting his eyes finally.

Castiel stopped breathing and pushed Dean away from him, walking over to his kitchen. He gripped the counter tightly and stared over at Dean. He looked smart, he always did. His slacks were dark and pressed crisp, his blazer clean and pressed with his hat slightly tipped in the front. Dean definitely would have been someone Castiel flirted with and would try to bed but he didn't know if he could. He was a murderer, someone Castiel was supposed to put cuffs on.

Dean sighed and walked over to him, stepping behind the detective and placing his hands on his hips. He leaned forward to whisper into Castiel's ear, "Choose, Castiel. Either you're with me or against me... I'll be back." Dean pressed a soft kiss against his temple before walking out of the apartment and flicking the collar of his jacket up to cover his chin and neck, shrinking into it some. The minute Dean left, Castiel slammed his fists against the counter. This wasn't supposed to happen, Castiel wasn't supposed to feel infatuated by someone in the Mafia. He wasn't supposed to second guess his entire life's morals and rules. Dean was never supposed to happen.


	3. Chapter 3

Hola, Amigos! Thanks for all of your lovely reviews and for loving the story so far! You guys are giving me so much motivation, it's amazing. This chapter is going to be a bit short but do not fret, the next chapter will be very nice, I promise. Also, my beta for this story hasn't replied to me yet and I've just been too excited to NOT share it! So sorry for tiny grammatical errors and such. If anyone is interested in being a beta for this story, please email me. Just had to get some things out of the way first. So here is chapter 3, enjoy!

xx

Dean was nervous and his palms were sweaty, looking around the luxuriously decorated room. Luis never was one to hold back with money, always eager to spend and flash cash. There were paintings on every wall, a desk with a box of his favorite cigars and gold plated accessories everywhere. It was big and roomy, but to Dean, it was extremely stuffy at the moment. Luis as called him over for a "quick talk". The thing about Luis though, he never just talked for fun.

"Dean! My man, the golden boy. You know, that's what the papers call you?" Luis said loud and obnoxiously, his body plopping down on the leather chair behind his desk, "The Golden Boy of New York City. Cause you could do no wrong." Luis took out a cigar from his case and swiped it under his nose, inhaling it's scent. After a moment of basking in the smell, he placed the cigar in his mouth and lit it up.

"I beg to differ..." Luis started, taking the cigar and resting in his chair. He turned a hard and critical gaze onto Dean, "It's been two months now Dean and... Castiel is still alive... Elaborate." Luis said, waving his hand around.

"Sir, I personally like to follow my targets before I do the job. Especially with cops." Dean started, puffing his chest out a bit to make him look not so nervous. In reality, this situation scared the shit out of him. There was never a single time that Dean had gotten in trouble with the Mafia and his boss, so this was foreign to him.

Luis nodded his head and waved to a chair that was in front of his desk, "Sit down, Dean..."

"Dean... I trust you. You're good at what you do and never have you failed me. When Sam was sick from pneumonia, I gave you all the money and medication you needed. When your Daddy kicked you out of Paterson, I gave you an apartment in the Bronx. When everyone else said you were too young, I said you were just right." Luis was standing up and walking around, his eyes gazing over an ugly painting that was on his wall, "But never have you disappointed me to regret my decisions with you."

Luis was now standing behind Dean and cleared his throat. "Show me your palm, will you?"

Dean held out his hand nervously, but not a single quack went through him. He was rock solid, dead set on keeping up his courageous front.

"Some gypsies said once, that you can tell a person's fate with their palm..." Luis said while looking over the wrinkles in Dean's hand. "Let's test that theory..." Slowly, Luis turned over his palm and laid his cigar flat on the front of his hand. Dean screamed and jumped to his feet, attempting to pull his hand back but it was held tightly by Luis.

"I'm not one to toy with, Dean. You have a week to finish your job or someone else will. And you will be... disposable. Now go." Luis scowled at Dean as he left the room.

xx

"What did he do!" Sam stared at Dean who was clutching his hand to his chest. The younger brother was cutting up an orange in the kitchen when his brother burst through the door, panting and sweaty from running. He nearly ran over to the sink and coated it in cold water, the humid air of spring not helping with the burn. There were specs of ash in the wound, blackening the area when water ran over it.

"He fucking gave me flowers, Sam, what do you think? Son of a bitch put his cigar out on my fucking hand!" Dean yelled back at his brother, glaring at him.

"Why did he burn you?"

"Because I'm not doing my job!"

"You mean the hit on Castiel?"

Dean went quiet, the only sound in the room being the running water from the tap.

"Dean what is going on? Tell me what is going on." Sam started, standing behind his brother.

"Sam, nothing is going on..." Dean mumbled back, staring at the drain.

"Bullshit! Dean, you just got burned cause you won't bump off a cop you've been stalking for two months now! It never takes this long!"

"I like him, Sam!" Dean finally shouted back, closing his eyes tightly.

"Like... like like him?" Sam asked, stepping to the side to look at Dean.

Dean looked back with a blank expression, nodding his head slowly. Sam whispered an "Oh..." and crossing his arms over his chest. Dean had never told Sam that he was interested in men as well as women since he never saw a situation before where he needed to tell him.

"So you like... guys..?" Sam started, a blush creeping up his expression.

"And women... I don't really care." Dean mumbled back, embarrassed by the conversation at hand.

"And... you like Castiel, the guy you have a hit on...?" Sam asked again, earning himself a glare from Dean, "Alright, alright... I just hope you know what you are doing." Sam walked away, shaking his head.

Dean groaned in response, taking in a long breathe before turning off the tap. He stared at the burn wound, felt it pulsating with pain. He simply shook his hand and grabbed his coat again, making his way back outside. Sometimes he wonders how he even got into this mess.

xx

December 15, 1925

"Dean, you stole from old Palecki's store? You know we can't go there, that's not our territory!" A kid name Blade shouted at him while they walked down Palm Leaf Ave. Dean was the sprouting age of 15, a full-fledged member in a gang for his part of town. He could fist fight for his life and was fast on his feet, always dazing his opponents. The most recent being the gang leader of the other side of Paterson.

"Yeah, Sam wasn't feeling well. Palecki had the medicine but wouldn't give it. So I took it." Dean said back, strutting down the street with confidence. Sam was sick with a word Dean couldn't say just right, his Dad both too lazy and poor to get the right medication for the youngest Winchester. Dean had no choice but to take what he needed to help his baby brother, determined to do anything to help him. Ever since their mother died, Dean promised himself that he would never let anything hurt his sibling. It was his way of coping, knowing that he had someone to protect and watch over. Sam was too young to understand but he gave Dean purpose. He knew that while Sam with him, no fire or anything could take him away. Even when their Dad spent all their money on illegal booze, he still found a way to make sure Sam was fed every night. Somewhere along the lines, he joined a gang to get help and money every now and then.

When word got around that Dean had gone into the other side of town, their gang leader saw it as a threat. So he did what any child would do, challenge him to a fight. Dean was approached at a grocery fair, looking around for things to buy for Sammy for dinner. A little kid, a small hat on his head and dirt under his nails.

"Dean Winchester? Alistair from the East said for you to meet with him at the field in front of school for a fight at 6PM tomorrow." He ran away right after, not bothering to hear a reply. Dean only rose an eyebrow and smirked, nodding his head. Now he was on his way, people constantly trying to stop him or offering their fists. He turned down all of them, this was his own fight and no one else's.

A half hour later, Dean had the leader of the East's shirt bunched in his hands. His fist made contact with his face repeatedly, dropping him after a moment. "Nice try, really. You might actually have a chance next time. Don't mess with us, got it?" Dean didn't wait for a reply and made his way out, being stopped by a teenager a few minutes later.

"We could use your fists, kid... come with us if you want to play with the big boys now."

xx

Dean showed up at Castiel's apartment at around 5 in the afternoon, tired and still hurting from the burn. After their first kiss in the empty apartment, Dean visited Castiel almost every other day. Together, they would kiss or talk about nothing. Dean slowly started to realize just how different Castiel was compared to the rest of New York's pigs. He was never able to really understand him though, never getting a chance to ask much about him. He decided to wind down at Cas' apartment, a place where he didn't have to worry about much just yet. That was, until he was met with a cold pair of silver bracelet's the moment he closed the door behind him. Dean stared at them for a moment, than at a pair of stunning blue eyes.

"What the hell, Cas?" Dean shouted, his eyebrows coming together.

"I can't do this anymore, Dean. I'm not some toy for you. I have a responsibility. No more of this."

Dean looked around the living room, noticing that it was empty. The usual sofa that took up half of the room was gone, the shaky table with the typewriter was missing, only scratches on the floor remand. Dean's eyes were wide and he stared at his detective, still processing the situation.

"I'm moving back to Chicago. I'm not meant for New York or you. Dean, we can't do this..." Castiel mumbled, looking away from him. Dean was speechless, letting himself be dragged out the door. Together, they made their way to Castiel's rusting car. Dean was seated in the passenger seat, still silent and shocked. In the back seat was all of the detective's stuff. His typewriter and clothes, all shoved into suitcases and bags.

"Don't do this, Cas..." Dean mumbled, staring down at his cuffed hands that were on his lap.

"I have no choice..."

"You always have a choice!"

"No, not always..."

"Castiel, look at me." Dean stared at the detective, Castiel only staring at his steering wheel silently, "You always have a choice. You will do what you want, not what everyone else wants. Cas, I know you don't want to do this so don't."

"You don't know anything about me, Dean! I'm a cop, I work for the country! You are a wanted man, I should have done this the first night I saw you!"

"Castiel, stop!"

"No! No more 'Castiel stop', no more! Dean, I'm not doing this. Absolutely not." Castiel started the car and began the route to the station. It would be a bit of a drive, his apartment wasn't that close to the station. The entire time, though, his hands strained against the steering wheel. Dean was still staring at him, his heart pounding ruthlessly under his skin. He was starting to wonder if Castiel could hear it's unforgiving beat, about ready to burst through his chest. The one person he started to trust, outside of Sam, was now taking him to basically his death. He hasn't heard any news from other captive gang members but he knew that was for a reason. A single tear fell down his cheek and he glared.

"So this is it. You're gonna be a good little soldier and ignore what you want from your life? Ignore what was meant to happen with us."

"Yes."

"I had a lot more respect for you, I thought you were different."

"Well you thought wrong. Dean, stop it. Stop trying, it's not going to happen."

Dean's heart sank, he swore he could hear it dragging under the car for a moment.


	4. Chapter 5

xx

He would never admit it or tell you why, but Dean's favorite flower was the Lavender. Mary, Dean's mother, had a Lavender garden while she was alive. When he was young, he would run through the backyard and smell the flowers in the air. Mary's blonde hair would sift and weave with the wind, her giant gardener's hat blocking the sun from her eyes. It was one of Dean's few memories of her, watching her garden while he played. It was something he would turn to think about when things started getting funky. Sometimes, if he really thought hard about it, he would swear up and down that he would smell Lavenders.

His heart was thumping hard in his chest, his eyes darting from the road in front of them to Castiel. Even now, while Dean was scared out of his wits for his life, he couldn't help but admire him. The tufts of dark hair was stringy and messy, surviving a long night of restless slumber. His skin was porcelain and the stubble of his sprouting facial hair tantalizing. Long elegant fingers curled around the steering wheel effortlessly but still with tension. Suddenly a shock of blue eyes were facing him for a brief moment, Castiel looking over at him. Dean was hunched forward a bit, trying his best to look at him. Castiel cursed under his breath and turned down an unnamed side street, stopping half way down. Suddenly he stepped out, slamming the door behind him. The same elegant fingers reached into a lock of dark black hair, seeming to be mumbling to himself. Dean had the perfect opportunity to just run out of the car right now but he felt as though his feet melted into the floor.

Suddenly the distressed detective made his way to the passenger side of the car and pulled the door open. Castiel glared at Dean and spoke with his gravely tone, "Get out." Cas stepped to the side so Dean could come out. The moment Dean took his last step out, Castiel took him by the collar of his button up and pressed him against the brick wall behind them, "Do you have any idea what you are doing?" Castiel mumbled with a hushed tone. His voice quivered, as though desperate to yell but wanted a sense of self control. His hands pushed Dean harder against the wall. "You are destroying everything I built up. I had goals and ambitions but you come into my life and screw everything up."

Castiel gave Dean a shove before letting go and turning around, a hand running through his hair while the other rested on his hip.

"Castiel, I-" Before Dean could even speak, though, Cas shoved his lips onto his. The kiss was heavy and full of teeth, Castiel's hands back on Dean's shirt collar. The energy was electric, the eager detective nipping and licking the thug's lips. Dean let out a strained groan and Castiel took the opportunity to explore. His tongue circled and teased, dragging across teeth and fighting for dominance. Suddenly, hips pressed against hips and Dean broke the kiss to press the back of his head against the wall with a stuttered moan.

"You come in with your..." Castiel bites the side of Dean's jaw, "Your teasing remarks and cocky grins." Dean doesn't know how to react, what to do with his hands and what to feel. One moment Castiel was definitely very mad at him and now he practically right on top of him.

"Castiel, I..." Dean pushed at his chest a little, "I don't understand what's going on..."

"How do you still not get it, Dean?" Castiel shouted while taking a step back from him, "I can't do it! I can't do my job, I have one of New York's most notorious gangsters literally at my fingertips and I can't do my job..."

"Well if it helps any, I can't my own god damn job either, Cas! Doesn't mean I'm gonna go dragging you up to my boss like a ham at Thanksgiving dinner!"

"If anyone ever found out about us..." Castiel started, looking down at a puddle of unknown liquid on the ground, sighing.

"Comes with the whole gangster thing, Cas. We're a never ending game of cops and robbers, we're meant to chase each other." Dean couldn't even understand his own words, exhaling a heavy breathe he wasn't aware he sucked in, "What could you possibly be expecting otherwise, run around holding hands and kisses on the cheek at the grocery store?"

Castiel was silent and shook his head, turning away from Dean to kick the back tire of his car. He was torn, that was obvious but he felt as though the answer should be easy. Dean was willing to accept what they had but Castiel was still stuck on the fact that he would lose everything he has ever worked for if discovered. With a nod, he looked back up at Dean and stared deep into him. It was all of nothing. He took the small step to get closer to the gangster again, resting his forehead against his before once again nodding, "I'll need help."

"I know that, wonderboy. You're not exactly the easiest person to date." Dean started, his tone growing silent after realizing what he said.

"So we're an item now?"

"Sure, Cas..."

Lavenders were Dean's favorite flower, purple and bright with summer life. For some reason, Dean started to think those fond memories with Mary and her garden. It calmed him and eased the stress from his shoulders. Meanwhile, a soft flutter of steps shuffled away.

"What could you possibly want from me, Leo?" Mark muttered through a giant cigar, the showgirls fluttering and giggling around him.

"Mr. Lipezki, you gotta hear this." A scrawny blonde boy came up next to Leo, a man wearing a pressed brown suit with a fedora.

"Aah, Tommy! What can I do for you, my boy?" Mark smirked and pulled Tommy close, even though he was much taller than Mark since he was seated. Mark was a don for an entire town, huge and growing with shopping malls and restaurants. Almost all of his brothers were linked in his little mob, controlling towns and districts with brute force. Mark was easily almost 300 pounds, a thick and booming voice with chubby sausage fingers. He was known for being a generally tender guy, forgiving and lenient when compared to his brothers. He was also the most formal and oldest of the brothers, so his opinion was usually one that never reconsidered.

"It's about Winchester, sir..." Tommy mumbled, his voice almost squicky.

"Winchester? I haven't heard from the boy in months. What do you got, Tommy?"

"Can we go in private, sir..?"

I'm really sorry about that delay, everyone! I just got a job with WALT DISNEY WORLD(whatwhat?) so I've just been adjusting to moving and crazy hours. Thank you for staying patient with me!

Short chapter, I know, but it's leading up. It is easy for me to believe that the next chapter will be the last. I wanted this to be A LOT longer but I am just too busy. :/

See you guys soon!


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